Water → tert-Butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate

HRID 44696Notes

Reaction equation

HRID 44696 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[O-]CC.[Na+].O.[N+:20]([CH3:23])([O-:22])=[O:21]>C(O)C>[OH:1][C:2]1([CH2:23][N+:20]([O-:22])=[O:21])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 53486300tert-Butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (52.65 g, 264 mmol) in nitromethane (21 mL) and ethanol (8 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 5.0 mL, 13.4 mmol). The mixture was stirred at rt and more ethanol (30 mL) was added. The mixture was sonicated for 15 min, stirred overnight, then sonicated again. To the mixture was added water (400 mL). The solid was isolated by filtration, washed with water (300 mL), and dried to yield tert-butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate as a white solid, 67.60 g (98%).

Workup

  1. customThe mixture was sonicated for 15 min
  2. stirringstirred overnight
  3. customsonicated again
  4. customThe solid was isolated by filtration
  5. washwashed with water (300 mL)
  6. customdried

Sources & evidence

ORD record
ord-5a774da83d594aa2967633177319fa78
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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